The Story of Jean Grae, One of Rap’s Greatest Lyricists, in 8 Songs

Jean Grae is a polymath in every sense of the word. She first rose to prominence in underground hip-hop circles as an MC, but a quick glance at her Patreon page reveals the plethora of hats she’s worn since: “Writing, producing, rapping, singing, directing, filming, editing, acting, comedy, hosting, cooking columns, (a lot of cooking) freelance writing, voiceovers, hairstyling, putting on plays, lecturing at prestigious universities, teaching children, hosting my own live talk show, live music shows, free hug stations, improv, scoring podcasts…” It’s a lot.

Born Tsidi Ibrahim to jazz musician parents in Cape Town, South Africa, Grae was likely always destined to become a performer. She grew up in New York City, first coming to America with her family when she was just three months old, amid racial turmoil in their home country. She attended the famed LaGuardia performing arts high school and studied music business at NYU before committing to music full-time. It’s been more than 20 years since she dropped her first verse on wax, and while Grae might not be a household name, you’d be hard pressed to find a rapper willing to battle her. Strictly lyrically, she’s one of the most gifted MCs ever.

Her latest LP, a collaboration with fiancé Quelle Chris called Everything’s Fine, is a masterpiece of rap performance, blending dark comedy, cathartic narrative, and even vaudeville with a hip-hop soul. The album is the product of someone trained in the art of lyrical supremacy, beaten down by leaks and shady record execs only to emerge stronger and wiser for a second act even more impressive than the first. It would be impossible to sum up her life and career in anything shorter than a book. But we’ve plucked some of our favorite tracks from her long and tumultuous career that paint a picture of how this singular artist has carved out her own lane and left her mark.

The Genesis

The Track: Natural Resource’s “Negro Baseball League” (1996)

Jean Grae has always had jokes. Her first MC name was a troll, chosen in hopes of starting an Abbott & Costello routine whenever she was introduced on stage. As What? What? she toured and recorded with DJ Aggie and Kobie Dixon as Natural Resource, making the gritty boom-bap that New York was becoming famous for. They lived in what Grae calls “‘The Real World’ for rap,” a house with a studio, 10 residents, and a rotating cast of MCs and DJs coming through to record.

On “Negro Baseball League,” the trio flips a music industry/sports metaphor into wry social commentary. Grae is as irreverent as ever, mocking players, umpires, and fans. She even manages to beat Colin Kaepernick to the punch by about a decade: “I'm not patriotic, so I won't sing the National,” she spits. Natural Resource would be in short supply, but Grae was just getting started.

The Guest Features

After Natural Resource wrapped up in 1998, she changed her pseudonym to Jean Grae, a nod to the X-Men’s most powerful psychic not named Xavier. As she prepped her debut, Attack of the Attacking Things, she cut a few memorable features that showcased her flair for narrative. In the wake of the Columbine massacre, Mr. Len’s “Taco Day” imagines a school shooting at the hands of the prom queen, who’s driven to violence by domestic abuse. The killer’s inner monologue evokes Eminem’s explorations of trauma and psychosis, as does the disturbing glee with which Grae seems to revel in recounting the violence. The character is at once both empathetic and completely unhinged, suggesting that no school shooting happens in a vacuum and ultimately providing a nuanced perspective on the interconnected nature of American violence.

Her contribution to Mr. Lif’s post-apocalyptic posse cut "Post-Mortem" is somehow even darker. Reading like a lost verse to Mase’s classic “24 Hrs. to Live,” Grae refuses to take her fate lying down, downing booze and pills, robbing, vandalizing, and impaling women with strap-ons. That it stands out as bleak while immediately following a verse from a famously grim El-P is evidence of how much she embraces the track’s doom and gloom.

The Chelsea

The Track: “God’s Gift” (2002)

By this point, Grae’s jazz singer mother had moved back to South Africa, so she had taken over the family apartment in the Chelsea Hotel. Her brother Tsakwe, a pianist, had left behind his production gear, so Grae was essentially moving into a home recording studio in a historic building full of other artists and weirdos. She wanted Attack of the Attacking Things to feel like a snapshot of her life at the time, so she built skits around phone conversations with her friend. Grae would later tell Underground Hip-Hop that she started recording the skits before she did anything else. “In my mind—in albums that I love—if there aren’t any skits in there to tie it together, then it doesn’t make sense to me,” she said.

While her inexperience behind the boards and a blown-out monitor led to inconsistent production and mixing, Grae offers a glimpse of her insanely high ceiling as an MC, foregoing vocal histrionics for a smooth flow with precise diction. She gets an assist on production from Masta Ace here on “God’s Gift,” taking on the voice of a narcissistic player over a stutter-step beat. It’s a caricature of every male rapper’s braggadocio sex fantasies, and a glimpse at Grae’s skill at character-building.

The Babygrande Fiasco

Grae’s sophomore LP, 2004’s This Week, for Babygrande Records was well-received critically and even made an appearance on the Billboard charts. But by 2008, Grae’s relationship with the independent label had deteriorated beyond repair. She’d already signed with Talib Kweli’s Warner Bros.-distributed label Blacksmith, but her old label still had the rights to unfinished verses and beats she’d worked on under contract—and they had every intention of squeezing as much cash as possible from them. First, Babygrande released The Orchestral Files, a sprawling smorgasbord of verses and loose songs they had the rights to; next was Jean Grae: The Evil Jeanius, a collection of verses set to beats by the production duo Blue Sky Black Death. Needless to say, Grae was not pleased, telling a Colorado alt-weekly, “I don’t even know those songs. You just took my vocals and beats and called it a new album? So, fuck Babygrande.”

Though it was first released in 2005 (on Guru’s Version 7.0), before the Babygrande situation fully escalated, “Power, Money & Influence” gives a glimpse into her view of the label: “If I gotta attend jail just to boost up the sales/I know a label owner that I'd love to bruise up for bail.” Three years later, shamelessly, Babygrande would include the track on The Orchestral Files.

The Leak

The Track: “My Story” (2008)

Jeanius is one of those records that was shrouded in myth before it even came out. The album, Grae’s third, leaked four years early with no track names, leaving file-sharing fans to guess at the titles and pester her with questions about songs that weren’t technically released. By the time Jeanius officially landed on shelves in 2008 (via Blacksmith), it was clear that these ill rhymes set to soul-bap beats (via producer 9th Wonder) had been well worth the wait.

The standout track, “My Story,” is an autobiographical tale about an abortion Grae had as a teen. The lyrics are visceral, describing the sights, smells, and sensations of the experience, from the anti-choicers calling for damnation outside, to the antiseptic aesthetic of the clinic inside. Sadly, in yet another tragedy of creative control, the song’s video was cut without her involvement, turning the most personal of experiences into something she didn’t even recognize. By the time it was released, Grae was so disillusioned by the industry that she had taken to Craigslist to offer her services as an MC, charging $800 for 16 bars.

The Fiancé (Quelle Chris Collabs)

The Tracks: “Don’t Be a Dick to the Waitstaff” (2014) and “The Prestige” (2017)

Everything’s Fine may be Grae’s first LP with Quelle Chris, but they’ve been writing about and with each other for years before they got engaged in 2017. They released a trio of “instructional albums” from 2014 to 2016, EPs comprised of running jokes seemingly inspired by all the annoying people the pair meets on the road and at home in New York. Chris features on a couple songs from Grae’s 2015 EP iSweatergawd, and they’ve made an audiobook, short films, and hosted talk shows together. Grae has always been funny, but they seem to bring out the best in each other’s humor, especially on Everything’s Fine, which feels like a salve for anxiety but also directly fueled by it.

On “The Prestige,” from Chris’ 2017 LP Being You Is Great! I Wish I Could Be You More Often, Grae serves up a healthy dose of sardonic resignation, rapping about “doing Crossfit in a Gowanus warehouse waiting for the apocalypse.” Because if we’ve learned anything about Jean Grae over the years, we know she won’t take the end of the world lying down.